| Arsenal FC v Manchester United FC 22/08/1999 | £6.00 | |
| Wolverhampton Wanderers FC v Wycombe Wanderers FC 24/08/1999 | £4.50 | |
| Fulham FC v Northampton Town FC 24/08/1999 | £4.00 | |
| Gillingham FC v Brighton & Hove Albion FC 24/08/1999 | £7.50 | |
| Notts County FC v Bury FC 24/08/1999 | £6.00 | |
| Queens Park Rangers FC v Cardiff City FC 25/08/1999 | £7.50 | |
| Skonto Riga v Chelsea FC 25/08/1999 | £6.00 | |
| Sheffield Wednesday FC v Derby County FC 25/08/1999 | £4.00 | |
| Arsenal FC v Bradford City FC 25/08/1999 | £2.00 | |
| Arsenal FC v Bradford City FC 25/08/1999 | £3.50 | |
| Arsenal FC v Bradford City FC 25/08/1999 | £4.00 | |
| Tottenham Hotspur FC v Leeds United FC 28/08/1999 | £5.00 |